Bistinospinosides A and B, Dimeric Clerodane Diterpene Glycosides from Tinospora sagittata

• Published in: Journal of Natural Products Vol. 80; no. 9; pp. 2478 - 2483
• Main Authors: Li, Wei, Huang, Chao, Liu, Qingbo, Koike, Kazuo
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 22.09.2017; American Chemical Society (ACS); Amer Chemical Soc
• Subjects: Chemistry, Medicinal; cycloaddition reactions; Diterpenes, Clerodane; Diterpenes, Clerodane - chemistry; Diterpenes, Clerodane - isolation & purification; Diterpenes, Clerodane - pharmacology; diterpenoids; Glycosides; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - pharmacology; Life Sciences & Biomedicine; Macrophages; Macrophages - chemistry; Macrophages - drug effects; Molecular Structure; Nitric Oxide; Nitric Oxide - analysis; Nitric Oxide - chemistry; Pharmacology & Pharmacy; Plant Roots; Plant Roots - chemistry; Plant Sciences; roots; Science & Technology; spectral analysis; Tinospora; Tinospora - chemistry; OLIV. GAGNEP; PLANTS; NEOCLERODANE DITERPENOIDS; CONSTITUENTS
• ISSN: 0163-3864; 1520-6025; 1520-6025
• DOI: 10.1021/acs.jnatprod.7b00324

Two dimeric clerodane diterpene glycosides, namely, bistinospinosides A (1) and B (2), were isolated from the roots of Tinospora sagittata. Their structures were elucidated by extensive spectroscopic data interpretation. The compounds feature an unusual 1,4-epoxycyclohexane ring in their structures and may be biosynthetically constructed via an intermolecular Diels–Alder [4+2] cycloaddition from the corresponding clerodane diterpene. The compounds were evaluated in a nitric oxide inhibitory assay using J774.1 macrophage-like cells.